Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
  • A01N59/26—Phosphorus; Compounds thereof

Definitions

• Fungicidal composition comprising a pyridylmethylbenzamide derivative and a thiazolecarboxamide derivative
• the present invention relates to novel fungicidal compositions comprising a pyridylmethylbenzamide derivative and a thiazolecarboxamide derivative.
• the present invention also relates to a method of combating phytopathogenic fungi by applying at a locus infested or liable to be infested such a composition.
• European patent application EP-A-1056723 generically discloses the possibility of combining pyridylmethybenzamide derivatives with known fungicidal products to develop a fungicidal activity.
• the present invention relates to a composition
• a composition comprising : a) a pyridylmethylbenzamide derivative of general formula (I)
• R 1 may be a hydrogen atom, an optionally substituted alkyl group or an optionally substituted acyl group;
• - R 2 may be a hydrogen atom or an optionally substituted alkyl group
• - R 3 and R 4 may be chosen independently from each other as being a halogen atom, a hydroxyl group, a cyano group, a nitro group, -SF 5 , a trialkylsilyl group, an optionally substituted amino group, an acyl group, or a group E, OE or SE, in which E may be an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or a heterocyclyl group each of which may optionally be substituted; - p represents 0, 1 , 2, 3 or 4;
• - q represents 0, 1, 2, 3 or 4; and its agriculturally acceptable optical and/or geometric isomers, tautomers and addition salts with an acid or a base; and b) ⁇ '-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazolecarboxamide; in a (a) / (b) weight ratio of from 0.01 to 10.
• N-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazolecarboxamide is a thiazolecarboxamide derivative fungicide also known as ethaboxam.
• ethaboxam N-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazolecarboxamide
• halogen means bromine, chlorine, iodine or fluorine
• alkyl means a linear or branched saturated hydrocarbon group containing from 1 to 6 carbon atoms
• alkenyl means a linear or branched hydrocarbon group containing from 2 to 6 carbon atoms and an unsaturation in the form of double bond
• alkynyl means a linear or branched hydrocarbon group containing from 2 to 6 carbon atoms and an unsaturation in the form of a triple bond
• alkoxy means a linear or branched alkyloxy group containing from to 1 to 6 carbon atoms
• acyl means a fornayl group or linear or branched alkoxycarbonyl group containing from 2 to 6 carbon atoms
• cycloalkyl means a saturated cyclic hydrocarbon group containing from 3 to 8 carbon atoms
• aryl means a phenyl or naphthyl group
• heterocyclyl means saturated, partially saturated, unsaturated or aromatic cyclic group containing from 3 to 8 atoms, which may be a carbon atom, a nitrogen atom, a sulphur atom or an oxygen atom.
• hetercoyclyl may be pyridyl, pyridinyl, quinolyl, furyl, thienyl, pyrrolyl, oxazolinyl; - the term "optionally substituted" means that the group thus termed may be substituted with one or more groups which may be halogen, alkyl, alkoxy, hydroxyl, nitro, amin, cyano or acyl.
• composition according to the present invention provides a synergistic effect.
• This synergistic effect allows a reduction of the chemical substances spread into the environment and a reduction of the cost of the fungal treatment.
• the term “synergistic effect” is defined by Colby according to the article entitled “Calculation of the synergistic and antagonistic responses of herbicide combinations” Weeds, (1967), 15, pages 20-22. The latter article mentions the formula:
• E represents the expected percentage of inhibition of the disease for the combination of the two fungicides at defined doses (for example equal to x and y respectively)
• x is the percentage of inhibition observed for the disease by the compound (I) at a defined dose (equal to x)
• y is the percentage of inhibition observed for the disease by the compound (II) at a defined dose (equal to y).
• composition according to the present invention comprises a pyridylmethylbenzamide derivative of general formula (I).
• the present invention relates to a composition comprising a pyridylmethylbenzamide derivative of general formula (I) in which the different characteristics may be chosen alone or in combination as being :
• R and R may be chosen independently from each other as being a hydrogen atom or an optionally substituted alkyl group. More preferably, R 1 and R 2 may be chosen independently from each other as being a hydrogen atom, a methyl group or an ethyl group. Even more preferably, R 1 and R 2 may be both hydrogen atoms.
• R 3 and R 4 may be chosen independently from each other as being a halogen atom, a hydroxyl group, a nitro group, an optionally substituted amino group, an acyl group, or a group E, OE or SE, in which E may be a alkyl, a cycloalkyl, a phenyl or a heterocyclyl group, each of which may optionally be subtituted. More preferably, R 3 and R 4 may be chosen independently from each other as being a halogen atom, a nitro group or a halogenoalkyl group. Even more preferably R 3 and R 4 may be chosen independently from each other as being a chlorine atom, a nitro group or a trifluoromethyl group.
• p may be 1 or 2. More preferably, p may be 2.
• q may be 1 or 2. More preferably, q may be 2; and its agriculturally acceptable possible tautomers and addition salts with an acid or a base. More preferably, the pyridylmethylbenzamide derivative of general formula
• composition according to the present invention comprises at least a pyridylmethylbenzamide derivative of general formula (I) (a) and dithianon (b) in an (a) / (b) weight ratio of from 0.01 to 10; preferably of from 0.05 to 5; even more preferably, of from 0.1 to 1.
• composition of the present invention may further comprise a third fungicide active ingredient (c).
• the fungicidal active ingredient (c) may be selected from azaconazole, azoxystrobin, (Z)-N-[ ⁇ -(cyclopropylmethoxyimino)-2,3-difluoro-6- (trifluoromethyl)benzyl]-2-phenylacetamide, (/?S)-2-(4-chlorophenyl)-iV-[3- methoxy-4-(prop-2-ynyloxy)phenethyl]-2-(prop-2-ynyloxy)acetamide, benalaxyl, benomyl, benthiavalicarb, biphenyl, bitertanol, blasticidin-S, boscalid, borax, bromuconazole, bupirimate, sec-butylamine, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorothalonil,
• the third fungicidal active ingredient may preferably be selected from phosphorous acid derivative, phosphorous acid itself, or alkali metal, alkaline-earth metal or metallic salts thereof. More preferably, the additional fungicidal compound may be chosen as being fosetyl-aluminium . Where the third active ingredient (c) as defined above is present in the composition, this compound may be present in an amount of (a) : (b) : (c) weight ratio of from 0.01 : 1 : 1 to 10 : 1 : 30; the ratios of compound (a) and compound (c) varying independently from each other.
• the (a) : (b) : (c) weight ratio may be of from 0.05 : 1 : 2 to 5 : 1 : 25; more preferably of from 0.1 : 1 : 3 to 1 : 1 : 20; the ratios of compound (a) and compound (c) varying independently from each other.
• compositions may be cited to illustrate in a non-limited manner the present invention : compound (Ia) with ethaboxam; compound (Ia) with ethaboxam and fosetyl-aluminium; compound (Ib) with ethaboxam; compound (Ib) with ethaboxam and fosetyl-aluminium; compound (Ic) with ethaboxam; compound (Ic) with ethaboxam and fosetyl-aluminium.
• composition according to the present invention may further comprise an other additional component such as an agriculturally acceptable support, carrier or filler.
• the term "support” denotes a natural or synthetic, organic or inorganic material with which the active material is combined to make it easier to apply, notably to the parts of the plant.
• This support is thus generally inert and should be agriculturally acceptable.
• the support may be a solid or a liquid.
• suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports may also be used.
• the composition may also comprise other additional components.
• the composition may further comprise a surfactant.
• the surfactant can be an emulsii ⁇ er, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants. Mention may be made, for example, of polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the above compounds containing sulphate, sulphonate and phosphate functions.
• the presence of at least one surfactant is generally essential when the active material and/or the inert support are water-
• Additional components may also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active materials can be combined with any solid or liquid additive, which complies with the usual formulation techniques.
• composition according to the invention may contain from 0.05 to 99% (by weight) of active material, preferably 10 to 70% by weight.
• compositions according to the present invention can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas
• compositions include not only compositions which are ready to be applied to the plant or seed to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions which must be diluted before they are applied to the crop. .
• the fungicidal compositions of the present invention can be used to curatively or preventively control the phytopathogenic fungi of crops.
• a method for preventively or curatively controlling phytopathogenic fungi of crops characterised in that a fungicidal composition as hereinbefore defined is applied to the seed, the plant and/or to the fruit of the plant or to the soil in which the plant is growing or in which it is desired to grow.
• the composition as used against phytopathogenic fungi of crops comprises an effective and non-phytotoxic amount of an active material of general formula (I).
• an effective and non-phytotoxic amount means an amount of composition according to the invention which is sufficient to control or destroy the fungi present or liable to appear on the crops, and which does not entail any appreciable symptom of phytotoxicity for the said crops. Such an amount can vary within a wide range depending on the fungus to be combated, the type of crop, the climatic conditions and the compounds included in the fungicidal composition according to the invention.
• the method of treatment according to the present invention is useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots.
• the method of treatment according to the present invention can also be useful to treat the overground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruits of the concerned plant.
• cotton Among the plants that can be protected by the method according to the present invention, mention may be made of cotton; flax; vine; fruit or vegetable crops such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp.
• Rosaceae sp. for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches
• Rosaceae sp. for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches
• Rubiaceae sp. for instance banana trees and plantins
• Rubiaceae sp. Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges and grapefruit); Solanaceae sp. (for instance tomatoes), Liliaceae sp., Aster aceae sp. (for instance lettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurb ⁇ taceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp. (for instance strawberries); major crops such as Graminae sp.
• Asteraceae sp. for instance sunflower
• Cruciferae sp. for instance colza
• Fabacae sp. for instance peanuts
• Papilionaceae sp. for instance soybean
• Solanaceae sp. for instance potatoes
• Chenopodiaceae sp. for instance beetroots
• horticultural and forest crops as well as genetically modified homologues of these crops.
• Powdery mildew diseases such as :
• Blumeria diseases caused for example by Blumeria graminis; Podosphaera diseases, caused for example by Podosphaera leucotricha; Sphaerotheca diseases, caused for example by Sphaerotheca fuliginea; Uncinula diseases, caused for example by Uncinula necator; Rust diseases such as : Gymnosporangium diseases, caused for example by Gymnosporangium sabinae;
• Hemileia diseases caused for example by Hemileia vastatrix
• Phakopsora diseases caused for example by Phakopsora pachyrhizi or Phakopsora meibomiae;
• Puccinia diseases caused for example by Puccinia recondita
• Uromyces diseases caused for example by Uromyces appendiculatus; Oomycete diseases such as :
• Bremia diseases caused for example by Bremia lactiicae
• Peronospora diseases caused for example by Peronospora pisi or P. brassicae
• Phytophthora diseases caused for example by Phytophthora infestans
• Plasmopara diseases caused for example by Plasmopara viticola
• Pseudoperonospora diseases caused for example by Pseudoperonospora humuli or Pseudoperonospora cubensis;
• Pythium diseases caused for example by Pythium ultimum;
• Leafspot, leaf blotch and leaf blight diseases such as :
• Cercospora diseases caused for example by Cercospora beticola
• Cladiosporum diseases caused for example by Cladiosporium cucumerinum
• Cochliobolus diseases caused for example by Cochliobolus sativus;
• Colletotrichum diseases caused for example by CoHetotrichum lindemiithanium;
• Cycloconium diseases caused for example by Cycloconium oleaginum
• Diaporthe diseases caused for example by Diaporthe citri
• Elsinoe diseases caused for example by Elsinoe fawcettii;
• Gloeosporium diseases caused for example by Gloeosporium laeticolor
• Glomerella diseases caused for example by Glomerella cingulata
• Guignardia diseases caused for example by Guignardia bidwelH
• Leptosphaeria diseases caused for example by Leptosphaeria maculans
• Magnaporthe diseases caused for example by Magnaporthe grisea
• Mycosphaerella diseases caused for example by Mycosphaerella graminicola; Mycosphaerella arachidicola; Mycosphaerella fijiensis; Phaeosphaeria diseases, caused for example by Phaeosphaeria nodorum;
• Pyrenophora diseases caused for example by Pyrenophora teres; Ramularia diseases, caused for example by Ramularia collo-cygni; Rhynchosporium diseases, caused for example by Rhynchosporium secalis; Septoria diseases, caused for example by Septoria api ⁇ or Septoria lycopercisi; Typhula diseases, caused for example by Typhula incarnata; Venturia diseases, caused for example by Venturia inaequalis;
• Root and stem diseases such as :
• Corticium diseases caused for example by Corticium gramimanim
• Fusarium diseases caused for example by Fusarium oxysporum
• Gaeumannomyces diseases caused for example by Gaeiimannomyces graminis
• Rhizoctonia diseases caused for example by Rhizoctoriia solani
• Tapesia diseases caused for example by Tapesia acuformis
• Thielaviopsis diseases caused for example by Thielaviopsis basicola; Ear and panicle diseases such as :
• Alternaria diseases caused for example by Alternaria spp.;
• Aspergillus diseases caused for example by Aspergillus flavus;
• Cladosporium diseases caused for example by Cladosporium spp.;
• Claviceps diseases caused for example by C laviceps purpurea; Fusarium diseases, caused for example by Fusarium culmorum;
• Gibberella diseases caused for example by Gibberella zeae
• Monographella diseases caused for example by Monographella nivalis; Smut and bunt diseases such as :
• Sphacelotheca diseases caused for example by Sphacelotheca reiliana
• Tilletia diseases caused for example by Tilletia caries
• Urocystis diseases caused for example by Urocystis occulta
• Ustilago diseases caused for example by Ustilago nuda; Fruit rot and mould diseases such as :
• Aspergillus diseases caused for example by Aspergillus flavus
• Botrytis diseases caused for example by Botrytis cinerea
• Penicillium diseases caused for example by Penicillium expansum
• Sclerotinia diseases caused for example by Sclerotinia sclerotiorum
• Verticilium diseases caused for example by Verticilium alboatrum
• Seed and soilborne decay, mould, wilt, rot and damping-off diseases Fusarium diseases, caused for example by Fusarium culmorum;
• Phytophthora diseases caused for example by Phytophthora cactorum
• Pythium diseases caused for example by Pythium ultimum
• Rhizoctonia diseases caused for example by Rhizoctonia solani;
• Sclerotium diseases caused for example by Sclerotium rolfsii;
• Microdochium diseases caused for example by Microdochium nivale; Canker, broom and dieback diseases such as :
• Nectria diseases caused for example by Nectria galligena; Blight diseases such as :
• Monilinia diseases caused for example by Monilinia laxa
• Leaf blister or leaf curl diseases such as : Taphrina diseases, caused for example by Taphrina deformans;
• Esca diseases caused for example by Phaemoniella clamydospora; Diseases of flowers and Seeds such as :
• Botrytis diseases caused for example by Botrytis cinerea; Diseases of tubers such as :
• Rhizoctonia diseases caused for example by Rhizoctonia solani.
• the fungicidal composition according to the present invention may also be used against fungal diseases liable to grow on or inside timber.
• the term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
• the method for treating timber according to the invention mainly consists in contacting one or more compounds of the present invention, or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.
• the dose of active material usually applied in the treatment according to the present invention is generally and advantageously between 10 and 2000 g/ha, preferably between 50 and 1500 g/ha for applications in foliar treatment.
• the dose of active substance applied is generally and advantageously between 2 and 200 g per 100 kg of seed, preferably between 3 and 15O g per 100 kg of seed in the case of seed treatment. It is clearly understood that the doses indicated above are given as illustrative examples of the invention. A person skilled in the art will know how to adapt the application doses according to the nature of the crop to be treated.
• the fungicidal composition according to the present invention may also be used in the treatment of genetically modified organisms with the compounds according to the invention or the agrochemical compositions according to the invention.
• heterologous gene encoding a protein of interest essentially means genes which give the transformed plant new agronomic properties, or genes for improving the agronomic quality of the transformed plant.
• compositions according to the present invention may also be used fore the preparation of composition useful to curatively or preventively treat human and animal fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by Aspergillus spp., for example Aspergillus fumigatus.
• fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by Aspergillus spp., for example Aspergillus fumigatus.

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• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Inorganic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 2006
  • 2006-02-09 KR KR1020077016928A patent/KR20070103006A/ko not_active Application Discontinuation
  • 2006-02-09 CA CA2597010A patent/CA2597010C/en not_active Expired - Fee Related
  • 2006-02-09 PL PL06723589T patent/PL1850669T3/pl unknown
  • 2006-02-09 PT PT67235895T patent/PT1850669E/pt unknown
  • 2006-02-09 ES ES06723589.5T patent/ES2529047T3/es active Active
  • 2006-02-09 EP EP06723589.5A patent/EP1850669B1/en not_active Not-in-force
  • 2006-02-09 KR KR1020137018865A patent/KR20130089671A/ko not_active Application Discontinuation
  • 2006-02-09 MX MX2007009468A patent/MX2007009468A/es active IP Right Grant
  • 2006-02-09 RU RU2007133805/04A patent/RU2007133805A/ru not_active Application Discontinuation
  • 2006-02-09 US US11/884,154 patent/US9215874B2/en not_active Expired - Fee Related
  • 2006-02-09 JP JP2007554528A patent/JP2008530048A/ja active Pending
  • 2006-02-09 WO PCT/EP2006/002580 patent/WO2006084773A1/en active Application Filing

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